Running Up That Hill
by RedHerring86
Summary: When John, CEO of Winchester Industries, is murdered, Crowley becomes the new legal guardian of the boys.Dean hates his life under Crowley's thumb and runs away, stumbling upon a salvage yard in SD.But he finds that escaping his old life isnt that easy.AU
1. Chapter 1

**Just to clarify: this is NOT a child abuse story. **

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><p>Watching as the casket was lowered into the ground, Dean wiped his tears away with his sleeve, his eyes red from crying excessively. Usually he would be ashamed at such a show of emotion, but today was different. Today was the funeral of his father. The man he looked up to, the man he admired most. Gone. Murdered. With his brother by his side, he stood next to the grave and mourned his father. A hand is placed on his shoulder and he looks up to see that everyone else has left. The hand is not a stranger, yet it is unfamiliar and gave no comfort. Dean looked up to see Crowley, the vice president of his father's company.<p>

"It's time to go now Dean. We have things to sort out."

Dean nodded, not trusting his voice. He didn't care about whatever Crowley had to say to him. He didn't care about anything right now. He looked down to his six-year old brother sobbing uncontrollably and took his hand. He was ten years old, and the only family he had left was the little boy clutching his hand next to him. He would later learn that his father had, through his will, left his company in the hands of Crowley. It was also decided that Crowley, their mother's brother, would become the legal guardian of the Winchester brothers.

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><p>RUNNING UP THAT HILL<p>

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><p>EIGHT YEARS LATER<p>

Dean grabbed the waist of the girl in front of him and pressed his mouth to hers. He pulled away panting for the air he was just previously denied and loosened the tie around his neck. Damn private schools and their dress code. Dean grinned and leaned in to kiss her again, just as eagerly as the last time. He moved to her neck as she lifted her chin to allow him more access.

"Are you sure we should be doing this? I thought you would be suspended if you were caught skipping class again?" she breathed.

Not bothering to stop kissing her neck, Dean groaned.

"Mhmm, baby, you're killing the mood. Don't worry about it, no one will find us," he answered between kisses. Minutes later, he pulled away at the sound of his phone ringing. Checking the caller-ID, he saw the name CROWLEY flashing across the screen. Pressing the 'ignore' button, he put his phone away and returned to what he was doing.

"Who was that?" she asked, only slightly curious as she was, well, a bit preoccupied.

"No one important." They backed up into the fence behind the football stadium bleachers and Dean allowed his hands to roam freely up her thighs, pushing up her skirt. Dean was having a good time until…

"Dean Winchester!"

The girl he was with yelped in surprise and quickly pushed herself away to straighten herself up. Looking over to see the assistant principal striding towards them, Dean sighed. So much for his fun.

"Ms. Summers get back to class, I'll deal with you later. As for you young man, you will follow me to my office."

Dean rolled his eyes but followed her back.

"I'll have you know that I contacted your guardian. This has gone on for long enough. And straighten your tie," she snapped

Once they entered the office, Dean was met with yet another friendly face.

"Damn it Dean. Do you really think I don't have anything better to do than come clean up your messes?"

"Meg, always a pleasure," he greeted. Meg was Crowley's errand girl. She was also a bitch.

"I've told you, its Ms. Masters to you."

The corner of Dean's mouth pulled up into a smirk, showing he wasn't about to correct himself. The assistant principal next to him frowned.

"I thought Mr. Crowley was going to come?"

Meg plastered a patient smile on her face. "Mr. Crowley has much more important things to deal with than a degenerate teenager."

"I'm 18!" Dean protested.

Ignoring Dean, the assistant principal continued. "Well I was hoping to discuss this with his legal guardian, but I suppose we'll make due. Please, Ms. Masters, Dean, have a seat," she gestured to the two chairs in front of her desk and sat down in her own. Meg shot him another dirty glare before sitting. "The last time Dean skipped class to do… questionable activities… I told him he would be suspended. I still stand by my previous decision. Now, this behavior not only affects Dean but his fellow students." The rest of her rant was just as interesting. Dean zoned out somewhere between "extremely irresponsible" and "will not be tolerated". The only good thing about the situation was that Meg seemed pissed. She clearly wanted to be there just as much as Dean did.

He snapped back to attention when he heard Meg mention his name. "Well thank you for your time, Dean, is there anything you want to say?" she said, shooting him a meaningful glare.

"Oh, uh, yeah," he cleared his throat, "sorry, it won't happen again." He had to force himself not to smile as the principal pursed her lips: he used that line every time he was caught.

"Get in the car," Meg snapped as soon as they were outside. The chauffeur was waiting for their return and opened the limo door for them. Dean felt himself being pushed inside and moved to the seat furthest away from Meg, sitting directly across from her. At the sound of her phone ringing, Meg whipped out her cell to answer.

"Masters… Yes I have him now… Suspended…" she laughed," You'd think so , wouldn't you?... No, he's not that smart…"

Dean narrowed his eyes at her. He turned to glare out the window, wishing he was anywhere but here. The rest of the car ride continued as such, Meg continued to talk to her friend on the phone, more than once making a reference to how annoyed she was at the situation and taking stabs at Dean's intelligence. Something about Meg just got under Dean's skin; he absolutely could not stand her. He would probably start throwing punches if Meg weren't a girl.

He loosened his tie and reached for his school bag once they neared the mansion. Dean wordlessly got out of the car once it stopped, eager to get away from the bitch.

"This better not happen again, Dean!" he heard Meg shout out the window. Not even turning around, he responded by flipping her off, still walking toward the house.

The house. He hated the house. Everything about it screamed Crowley. Everywhere he went was a constant reminder of the life he hated. He went into his room to change into sweatpants and a t-shirt and decided to go to the gym and work out his frustrations.

"Mr. Winchester, is there anything I can get for you?"

Dean tensed; he almost made it to the gym without being bothered. Taking a deep breath to try and bury his frustration, he reminded himself that this woman was just doing her job. He failed.

"You're new here, and I get that, but I'm pretty sure that I've told you before to call me Dean. And another thing, I don't need you, or anyone else for that matter, to follow me around and wipe my ass for me. I'm a big boy now, I can do it myself. I promise you, it wont kill me. So for the last time, no, I do not need anything except for five freaking minutes where someone isn't breathing down my neck. Can you do that for me?"

She stood there in shock before fumbling with her words. "I'm sorry Mr. Wi- Dean. It won't happen again."

Dean ran a hand over his face. Now he felt bad on top of his frustration. "No, I'm sorry. It's just I'm a little frustrated right now, but I didn't mean to take it out on you." He forced a smile and the maid gave him one back.

"I'll be sure to tell the other maids you don't want to be bothered."

Dean only smiled back at her. They already know not to bother me at all. Finally making it to the gym in the west wing of the mansion, he slipped on his gloves and began beating into a punching bag. He only paused when he saw Sam come in.

"Hey Sammy," he greeted, continuing to lay it into the punching bag.

"Hey Dean," he set his backpack down and started to take out his homework. "So I heard you were suspended again. What was it for this time?" Sam asked nonchalantly.

"Skipping," he grunted.

Sam rolled his eyes but didn't say anything more about it. Dean gave a final jab into the bag, bent down to grab his water bottle, and then went to go sit against the wall next to Sam.

"Guess what?" Sam challenged as Dean drank from his water bottle. "Y'know that test I was concerned about? Well…" he flashed a packet of papers with a 100% scrawled across the top in red ink, along with a huge grin.

Dean returned the grin, grabbing for the paper. "See, I told you not to worry. You're too much of a geek to not do good," he said, ruffling Sam's hair in a playful manner. Sam began swatting his hands at his to stop him, so Dean moved his arm around Sam's shoulders in a kind of half-hug.

"It's awesome, Sammy. I knew you'd do good."

Sam's smile grew at the praise. He looked away a moment before looking back to Dean and wrinkling his nose. "Dude, you reek," he complained, but made no move to shrug off Dean's arm.

Dean looked down to his sweaty pits and leaned in to take a small whiff. "You kidding me? This is how a real man smells. Take it in while you can, there's no way you'll ever smell this good."

"Whatever, jerk."

"Bitch." Dean took a last swig of his water bottle and stood up. "I don't know about you, but I'm hungry. You want some food?"

"I could eat." A mischievous grin crossed his face. "Race you to the kitchen."

"You want me to kick your ass in a race? Alright then, say when."

As soon as Sam said the word, they both bolted out the door. Dean pushed Sam aside so he could get out the door first, and grinned as he ran down the hallway when he heard Sam whine "No fair Dean!"

Dean pounded down the hallways he'd known since he was 10, dodging the occasional maid or servant. He whipped his head around to see Sam following closely on his tail and started laughing at the concentration that was etched on his brother's face. Sam didn't lose the look of concentration but started laughing too, just because the laughing was so contagious. Dean turned around and saw his exit, the steps that led down to the main floor. He jumped clear across the first set of steps to land on the platform, then took another step before he was jumping down the next clump of stairs. He took a quick glance back to see that Sam was no longer following him. He must have decided to wait for the next set of steps, bringing him around a different way. He raced through the house to the right wing and finally reached the kitchen. He looked around to see that he beat Sam, and then took a moment to catch his breath. He started digging in the fridge when he heard his brothers labored breaths behind him.

He sighed when he saw Dean was already there. "What way did you go?"

"The better way apparently," he chuckled. "I took the way that passes by the rec room. What made you so slow?"

"I passed by the pool and slipped on some water," he laughed at himself in tired breaths. "I'm going to beat you one of these days."

"Keep dreaming." Scanning the fridge, he weighed his options. He looked up when he heard an older man's voice enter the room.

"Ah, Sam is there anything I can get for you?" the servant asked. He froze however, when he saw Dean.

"Naw, that's alright I think Dean is going to make something. Thanks though Jerry."

"My apologies Dean, I didn't see you there. Very well then, I'll be around if you need me." Sam gave him a smile and Dean just grunted and looked back into the fridge.

"You could be nicer to them you know."

Dean sighed and pulled out some eggs. "I'd be nicer if they weren't so annoying. Always asking me if I need something, or if there's anything they can do. I don't need someone to hold my hand when I walk around the house."

"Well I think most of them try to give you a five mile radius anyway. You've made it pretty clear to them all you don't want them around."

"Not clear enough apparently. Do you want eggs?" he asked, changing the subject.

Sam sighed knowing exactly what Dean was doing but consented to the eggs anyway. Dean cracked a couple eggs in the pan and started making scrambled eggs. Once they were done he took out a plate for Sam and dumped the eggs on it. He then cracked a couple more and proceeded to make himself a plate.

"So why were you skipping this time?" Sam asked, shoving some eggs in his mouth.

"Julie Summers," was all Dean needed to reply.

Sam scoffed. "You're such a man whore."

"Don't be jealous Sammy; you'll get a girl someday."

"I can get girls," he whined.

"Oh, so you mean to tell me that you've finally asked that Sarah chick out on a date? Y'know, the girl you've been pining over for weeks now."

"I have not been pining," he flushed. "And the right moment hasn't come up yet."

"Well what are you waiting for, man? Just go and ask her to a movie. Girls like guys with confidence. Try not to show her your nerdy side too much though." Dean laughed through his eggs when Sam gave him a punch to the arm for that comment.

Once they were finished, Dean grabbed Sam's plate. "Alright, get outta here. Go do your homework."

Dean washed both their plates and set them back in the cupboard. He then ran up the stairs to take a shower to wash off the sweat from the gym. Afterwards, he headed toward the garage to work on his car. It was a beautiful 1967 Chevy Impala, his pride and joy. It was his father's car, before he died, and they had been working on it together. They were never able to finish it. He was buried deep in oil when he heard his name being called.

"Winchester."

Dean spun around to see two of Crowley's goons standing in the doorway, looking directly at him. Dean sighed; he knew this was coming. "What can I do for you boys?"

"Mr. Crowley would like to see you."

"Is that so?" he sighed, wiping his hands clean of oil.

"Now."

"Well since you boys asked so nicely, how can I resist?" Shutting the hood of the car, he took his time grabbing the cloth and to cover the car again. He walked to the door past the two men. He didn't need to ask where Crowley was. The only time he talked to Crowley was in his office.

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><p><strong>Please leave a review =]<strong>

**Oh and don't worry, there are more characters to come. Obviously Crowley is introduced in the next chapter. Bobby won't appear until a couple more chapters, but he's got a major part. Cas, Ellen, Jo; the gang's all here. If you want to see anybody else... well I'm open to suggestions**


	2. Chapter 2

He heard him before he saw him. Dean walked into the office, closely followed by the two men.

"Well I want this account…. You better bloody well make it happen then!" he slammed the phone on the receiver.

"Careful now Crowley, mind your blood pressure."

"Dean, you arrogant little prick. How many times do I have to tell you to stay in the goddamn classroom?"

Dean pretended to think about it for a second. He held up his hand and started lifting up individual fingers like he was counting. Crowley slammed his hands on his desk.

"That was a rhetorical question you insufferable moron." He got up out of his chair and walked up to Dean, invading his personal space. Dean tensed but didn't move an inch, not letting Crowley intimidate him. "Do you have any idea how bad it looks every time I have to send someone to pick you up?" he dropped the volume of his voice yet there was still fury behind his words. "Do you have any idea how embarrassing it is to have to clean up your messes?"

"I'm sure you're going to tell me"

"Ever since the god-forsaken day they left you in my care you've been nothing but a pain. In. My. Ass." he said, enunciating the last four words by poking him in the chest each time. He glared at Dean, looking him directly in the eye, only to see defiance surging through them. "Another thing, why didn't you answer me when I called you?"

"I was busy at the moment."

"You were busy at the moment? Allow me to get this straight. When the school called me wondering where the hell you were, I decided to call you to tell you to get in the goddamn classroom. And you didn't answer because you were too busy getting it off with some whore outside on the bleachers. Did I get that right?"

"No, actually, it was on the fence outside the stadium. We were going to go for the bleachers because they had more cover, but then we just couldn't wait anymore."

Silence.

"You think you're funny" he deadpanned. He shifted his eyes to his two thugs behind Dean. "He thinks he's funny."

The sound of a sharp slap reverberated though the room, and Dean felt the sting on his left check. Enraged, he clenched his fist and moved to punch Crowley across the face in retaliation. However, before he could hit his target, his forearms were grabbed by Crowley's men. He struggled in the men's hold briefly before Crowley was in his face again.

"Well let me tell you how funny I think you are. Every time you decide to do something stupid, you're putting my name and my reputation on the line."

"I don't have your name you dick."

"Allow me to explain something to you. Because you are under my care-"

"Oh is that what you call it?"

"Because you are under my care," he insistently continued, "when the public sees you as the moron of the month, it reflects badly on me. Understand? And every time something like this goes on your poor excuse of a record, I have to pay some college a larger sum to even consider taking your sorry ass in next year. So the next time you decide to dick around with my name, think again."

"Who says I'll go to college next year?"

Crowley paused to look at him. Then he started laughing. "Oh my god, your serious." He continued laughing. He then turned deadly serious. "Oh you're going. The press would have a field day if I don't send you to college. Unless you want to go live on the streets, you'll do as I say."

"Like Hell I will"

"Goddamnit Dean what am I going to do with you?" The question hung in the air as no one spoke. Crowley scoffed. "If your father were still alive he'd be extremely disappointed in you."

Dean glared at him. That was a low blow. Worst of all, he couldn't deny it. Maybe his dad would be disappointed in him. He knew he could never be the man his father was.

Turning to the goon squad behind Dean, Crowley motioned to them. "Get this sack of shit out of my face."

Once the two thugs brought him out into the hallway, Dean angrily shrugged them off. "I can walk by my goddamn self."

He charged up to his room and slammed the door. He stood fuming for a moment, despising Crowley for everything he was. "Damn it!" he hissed, punching the wall. He glared at the hole in the wall he made, wishing instead that it could have been Crowley's head.

"Dean?" came a small voice outside his door.

Taking a deep breath, he closed his eyes, willing himself to calm down. He walked over to his door and swung it open to find his brother standing in the doorway.

"Hey Sammy."

"Is everything okay Dean? I heard a loud noise…" he asked nervously, knowing how Dean usually responded to that kind of a question. His eyes widened when he saw the hole in the dry-wall, about the same size as a fist. Dean closed the door more so only he was visible, and Sam could no longer see in the room.

"Everything's fine Sam."

"Did you get in a fight with Crowley again?"

"Nothing happened, go do your homework."

Sam paused, knowing he couldn't get Dean to talk if his brother didn't want to. "Can I do my homework in your room?"

Dean gave a sigh. For a moment Sam thought his brother would deny him. He didn't always do his homework in Dean's room, but it did happen frequently.

"Yeah, alright. Go get your school bag."

Sam scurried to his room two doors down, grabbed his books, and returned to Dean's room. He noticed that there was no longer a hole in the wall, and there was an ACDC poster that was about two feet from its original spot.

It was quiet for a little while, Dean flipping through a car magazine and Sam doing his homework.

"You want to talk about it?" Sam asked, figuring enough time had gone by for Dean's anger to settle.

"Talk about what?" he replied, his eyes never leaving the page of the magazine.

Sam rolled his eyes. "C'mon Dean, I know something happened between you and Crowley. I'm not an idiot."

"No, you're too damn smart for your own good. Besides, there's nothing to talk about."

"Dean…"

"What do you want me to say Sam? It's nothing that we haven't talked about before. Crowley's a dick. End of story."

"What was it about this time?"

Dean looked up from the page he was reading. Sam just wasn't going to back off was he? He closed the magazine and rubbed his hand over his face. "It started as me skipping then ended as what I would do next year."

That piqued Sam's interest. "And?"

"And… I don't know." He sighed deeply. "I just don't know. Crowley wants to send me to some hoity-toity rich school to keep his rep up."

"But you'll be getting away from him. Isn't that what you want?"

"Going to some bitch school isn't getting me away from him, it's just falling in line, doing what he wants. All he has to do is throw money at people and they jump-to. I can't keep living this life Sam."

A moment of silence passed as neither of them knew what to say next.

"Hey, when's your next soccer game?"

Sam saw the subject change for what it was but went along with it anyway.

"Next Tuesday. 5:00."

Dean nodded in affirmation. "I'll be there," he promised, returning to his magazine.

Sam smiled. Really it was nothing new; Dean went to all his games.

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